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Kepone

Kepone
Names
IUPAC name
decachloropentacyclo[5.3.0.02.6.03.9.04.8]decan-5-one[1]
Other names
Chlordecone
Clordecone
Merex
CAS name: 1,1a,3,3a,4,5,5,5a,5b,6-decachlorooctahydro-1,3,4-metheno-2H-cyclobuta[cd]pentalen-2-one
Identifiers
 YesY
ChEBI  N
ChEMBL  YesY
ChemSpider  YesY
EC number 205-601-3
Jmol-3D images Image
KEGG  YesY
PubChem
UNII  N
Properties
C10Cl10O
Molar mass 490.633 g/mol
Appearance tan to white crystalline solid
Odor odorless
Density 1.6 g/cm3
Melting point 349 °C (660 °F; 622 K) (decomposes)
0.27 g/100 mL
Solubility soluble in acetone, ketone, acetic acid
slightly soluble in benzene, hexane
log P 5.41
Vapor pressure 3.10−7 kPa
Thermochemistry
764 J/K mol
-225.9 kJ/mol
Hazards
Main hazards carcinogen[2]
Flash point Non-flammable[2]
Lethal dose or concentration (LD, LC):
LD50 (Median dose)
95 mg/kg (rat, oral)
US health exposure limits (NIOSH):
PEL (Permissible)
none[2]
REL (Recommended)
Ca TWA 0.001 mg/m3[2]
N.D.[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N  (: YesY/N?)

Kepone, also known as chlordecone, is an Stockholm Convention on Persistent Organic Pollutants as of 2011.

Contents

  • Toxicology 1
  • History 2
    • Case studies 2.1
      • James River estuary 2.1.1
      • French Antilles 2.1.2
  • In popular culture 3
  • Synthesis 4
  • References 5
  • External links 6

Toxicology

The LC50 (LC = lethal concentration) is 0.022–0.095 mg/kg for blue gill and trout. Kepone bioaccumulates in animals by a factors up to a million-fold. Workers with repeated exposure suffer severe convulsions resulting from degradation of the synaptic junctions.[3]

History

In the US, kepone was produced by

  • Terradaily: Pesticide blamed for 'health disaster' in French Caribbean
  • EPA releases a Toxicological Review of Kepone (External Review Draft) for public comment - 01/2008
  • CDC - NIOSH Pocket Guide to Chemical Hazards

External links

  1. ^ IUPAC Agrochemical information (http:/m.herts.ac.uk/aeru/iupac/1293.htm)
  2. ^ a b c d e
  3. ^ a b c Robert L. Metcalf "Insect Control" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Wienheim, 2002. doi:10.1002/14356007.a14_263
  4. ^ Stockholm Convention. Listing of POPs in the Stockholm Convention: Annex A (Elimination). 2011; Available from: http://chm.pops.int/Convention/The%20POPs/tabid/673/language/fr-CH/Default.aspx.
  5. ^ Jack Cooksey, "What's in the Water?", Richmond Magazine, June 2007, accessed 13 June 2012
  6. ^ Durimel, A., et al., pH dependence of chlordecone adsorption on activated carbons and role of adsorbent physico-chemical properties. Chemical Engineering Journal, 2013. 229: p. 239-349.
  7. ^ Wong, A. et C. Ribero (2013). Alternative agricultural cropping options for chlordecone-Polluted Martinique. Revue Etudes Caribéenens, n° 26, [1].
  8. ^ European Journal, Deutsche Welle, 26 May 2010.[2]
  9. ^ Survey of Industrial Chemistry by Philip J. Chenier (2002) page 484.

References

Kepone is made by dimerizing hexachlorocyclopentadiene and hydrolyzing to a ketone.[9]

Synthesis

  • Kepone was the name of an American indie rock band from Richmond, Virginia formed in 1991.
  • The Dead Kennedys recorded a song named "Kepone Factory", a satire of the controversy surrounding Allied Signal and their negligence regarding employee safety, for their 1981 album In God We Trust, Inc.. Written in 1978, the song was originally titled "Kepone Kids".

In popular culture

The French island of Martinique is heavily contaminated with kepone,[6] following years of its unrestricted use on banana plantations.[7] Despite a 1990 ban of the substance by France, the economically powerful planter community lobbied intensively to gain the power to continue using kepone until 1993. They had argued that no alternative pesticide was available, which has since been disputed. Similarly, the nearby island of Guadeloupe is also contaminated, but to a lesser extent. Since 2003, the local authorities restricted cultivation of crops because the soil has been seriously contaminated by kepone. Guadeloupe has one of the highest prostate cancer rates in the world.[8]

French Antilles

Due to the pollution risks, many businesses and restaurants along the river suffered economic losses. In 1975 Governor Mills Godwin Jr. shut down the James River to fishing for 100 miles, from Richmond to the Chesapeake Bay. This ban remained in effect for 13 years, until efforts to clean up the river began to get results.[5]

James River estuary

Case studies

[4]

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